Holiday rentals in Monticello

Bluegrass Gables: Lake Cumberland Cottage

Relax in the forest is this amazing 4bd/2.5ba cottage. Only minutes to the Ramsey Point boat ramp, this is your base for your Lake Cumberland vacation. Bring your boat; ample parking onsite. Don't have a boat? No problem, Beaver Creek and Conley Bottom marinas are close by. House features modern amenities and a fully stocked kitchen. Enjoy the fireplace indoors or the firepits outdoors. Forest views and fresh air galore await you, especially from the hot tub! Absolutely no smoking inside or out.

The Big Red Barn at LCK

Enjoy the lake or some quiet nature time in this secluded Barndominium on approx. 3 acres in the woods. Near Conley Bottom with plenty of room to park your boat trailer. Enjoy nearby public access to the lake, 5 minute drive to Conley Bottom Resort, or nearby Daniel Boone National Forest, Cumberland Falls, or some Pool Hall burgers in Downtown Monticello, Kentucky. Property is brand new and offers large rooms, well appointed kitchen, and walk in showers. Great covered porches and fire pit!

The Lake House at Beaver Creek

1 mile from marina Up to 8 people max allowed in rental NO pets allowed. $500 charge if suspected 4 beds: 1 KING 2 QUEENS plus a QUEEN size pull out sleeper sofa 2 full baths, living area, Free WiFi, local cable, fully equipped kitchen, laundry room, spacious deck, fire pit, gas & charcoal grill & more Plenty of parking for several vehicles, boats & trailers Policies: NO pets NO smoking NO parties or events of any type allowed Must be 23 years or older to reserve 2 night min. stay

Peaceful Getaway near Conley Bottom & Burnside

Welcome to our countryside getaway nestled on almost 5 acres within 5-20 miles of Burnside, Lee's Ford, and Conley Bottom Marinas. Enjoy the day on Lake Cumberland. Come back to relax, eat, drink & be merry. Gather around the outside barbecue area and fire pit or snuggle up inside next to the fireplace, playing games or watching a movie. Whether you are on a couple's retreat, fishing buddy's getaway, or family vacation - the house and outdoor area provide plenty of room to relax and enjoy.

Tiny LakeView Cottage~Pets! 1 nights available

We welcome your fur babies!! Kayaks available! Ice maker! Coffee pot w/coffee & creamer! Adorable, cozy tiny house with two decks & bonfire pit overlooking Lake Cumberland! It is located in Monticello, Ky, in a rural part of the area. It’s about 12 minutes to town. There is very close (driving distance) swimming access, kayaking, boating, boat ramps, fishing & marinas. On a dead end street, so very peaceful. Kayak rental is available for $25. per day/per kayak. Pet fee $50/$75 per stay.

Cottagey-Cabin, Private~Firepit! July Books Fast!

Serenity, tranquility & an inner peace is what you'll feel upon entering! Our 3-level, 4BR, 2BA cottagey Cabin accommodates 8 guests and boasts a seasonal view of CONLEY BOTTOM MARINA from its secluded, private, wooded lot! Inside, the warmth of natural woods will envelop you! The chef in your group will love the adorable kitchen equipped with every imaginable gadget, spice & cooking basic! Appointed in Cottagecore design, SERENITY RIDGE is the perfect blend between yesterday and today!

HOT TUB~ Fire Pit~ KING Ensuites~ Boat Ramp

Escape to Barndo Bliss, a newly built 4bd/3.5ba retreat nestled in Lake Cumberland's serene forests, just 1.2 miles from Ramsey’s Point boat ramp! Perfect for families and friends, this home features TWO luxurious King En-suites. No boat? No problem! Nearby Beaver Creek Marina offers rentals. Enjoy evenings by the large firepit surrounded by nature, perfect for s'mores, and unwind in the luxurious spa. Experience the tranquility of Lake Cumberland—book your stay at Barndo Bliss today!

The Cozy Cabell Cottage

It’s time for an adventure at our vacation rental, Cabell Cottage. With Lake Cumberland only 5 minutes away via the Cabell landing....really your boat is 5 minutes from being in the water; the cottage can be your base for all things fun on the lake (swimming, boating, and fishing). Did I CATCH your interest with fishing. However, if it’s a retreat you seek, the cottage is also for you as it sits in a quiet, very pretty, rural area of Wayne County, Kentucky, where 5 can sleep easily.

Lakeside Lodge Cabin

Experience the ultimate Lake Cumberland getaway at Lakeside Lodge. Nestled in Kentucky's natural beauty, this cozy cabin is perfect for families or small groups. Enjoy mornings surrounded by nature and evenings by a warm fire. A quick 5-10 minute walk leads you to a private neighborhood beach and boat ramp, making lake access effortless. Whether you’re hiking forest trails or exploring the water, Lakeside Lodge offers the perfect blend of comfort and adventure. Book your stay today.

D&D Cabin at Lake Cumberland *Pets Welcome*

Our cabin is a cozy place to relax and enjoy with the whole family. It is centrally located in Monticello, Ky. There is 2 parking areas to accommodate guest and boat parking. We are 5 minutes from Walmart and Black Stallion Steakhouse. Conley Bottom and Beaver Creek Resort is within 15 minutes. Nearby are multiple docks for fishing. We have an outdoor grill and picnic table with privacy fence. Marina Rowena is 28 minutes away. As well as Safe Harbor Marina is 25 minutes from here.

Hidden Creek Schoolhouse

Not all escapes are found on maps; some are found in time. Tucked into a quiet hollow just about 20 minutes from Dale Hollow Lake and Lake Cumberland, this 1919 schoolhouse offers a slower summer rhythm. Sunlight filters through original wood floors, the seasonal creek hums nearby, and fireflies dance at dusk. Spend your days on the water, then return to stillness. Hidden Creek is a storybook stay you step into, not rush through. Evenings stretch long under starlit skies.

Lake House "Dar Bida" Monticello

Forget your worries in this spacious, nearly 4,000 sq ft, and serene space. You will enjoy the silence and magnificent view on Lake Cumberland. "Dar Bida" is the ultimate place to relax and enjoy time with your family or friends. Lake Cumberland offers plenty of possibilities for outdoor activities such as paddling, boating and fishing. Two boat ramps are within 5 miles and boats can be stored at a dedicated boat storage area within the gated residence.